Methylamine → 5-Thiazolecarboxamide, N,4-dimethyl-2-(3,4,5-trimethoxyphenyl)-

HRID 637705Notes

Reaction equation

HRID 637705 reaction equation
CN.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:15]2[S:16][C:17]([C:21]([O:23]CC)=O)=[C:18]([CH3:20])[N:19]=2)[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12].COC1C=C(C=C(OC)C=1OC)[C:31]([NH2:33])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.ClC(C(C)=O)C(OCC)=O>C(O)CCC.C(O)C>[CH3:20][C:18]1[N:19]=[C:15]([C:7]2[CH:6]=[C:5]([O:4][CH3:3])[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=2)[S:16][C:17]=1[C:21]([NH:33][CH3:31])=[O:23]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 11858Ethyl 2-chloroacetoacetateHCID 14817Phosphorus sulfide (P2S5)HCID 18334Benzamide, 3,4,5-trimethoxy-HCID 12813041HCID 12813041, compound

Product 1

HCID 30680675-Thiazolecarboxamide, N,4-dimethyl-2-(3,4,5-trimethoxyphenyl)-Yield 60%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 702EthanolSolvent

Procedure

Into a mixture of 80 ml of 40% solution of methylamine and 420 ml of ethanol, 16.9 g of ethyl 2-(3,4,5-trimethoxyphenyl)-4-methylthiazole-5-carboxylate which had been prepared by heating a mixture of 3,4,5-trimethoxybenzamide, phosphorus pentasulfide, ethyl α-chloroacetoacetate and n-butylalcohol under a reflux condenser for 5 hours was dissolved and the solution was left for 10 days at room temperature. Then the solution was condensed to solid under a reduced pressure. The thus obtained residue was recrystallized from an aqueous ethanolic solution to obtain the object as colourless minute aciculate melting at 177.5° to 179.5° C. in an amount of 10.5 g corresponding to the yield of 60%.

Workup

  1. customhad been prepared
  2. temperatureby heating
  3. dissolutionwas dissolved
  4. customcondensed to solid under a reduced pressure
  5. customThe thus obtained residue was recrystallized from an aqueous ethanolic solution
  6. customto obtain the object as colourless minute aciculate melting at 177.5° to 179.5° C. in an amount of 10.5 g corresponding to the yield of 60%

Sources & evidence

ORD record
ord-88972b2fef914bbaaa5ffcc4341933ee
Source dataset
uspto-grants-1985_12
Patent number
US04558059

Reaction notes

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